Misadventures in Matchmaking
by Kittyaceres
Summary: Dean comes out to his family on his eighteenth birthday. They try to set him up with the waiter, his boyfriend Castiel.


Dean reluctantly filed into the restaurant after his parents. This was a fancy place, one that took reservations, and today was Dean's eighteenth birthday. You didn't have to make reservations, but Dean's family had already taken care of that. Unfortunately, that meant that they couldn't change the day that they came here. Dean wished that they could. That way, his boyfriend could join them. He'd been planning on introducing his family to Castiel and simultaneously coming out as bisexual to them. His plans had been aborted when he'd found out that Castiel had to _work_ tonight. When Dean had shared his plans with Castiel, Castiel had cryptically promised that it would all work out in the end. Whatever _that_ meant.

Now they were seated at their table. The hostess had taken their drink orders. Dean looked down glumly at the menu.

"What's wrong, Dean?" asked Mary.

"I just…oh, it's nothing," Dean sighed. "Nothing that can be fixed now."

"What, are you upset now that you're all grown up," teased Sam.

"Ha! I'm glad I'm no longer a baby like you!" Dean stuck out his tongue.

Their parents chastised them for bickering and rolled their eyes. "Eighteen years old and still a child," muttered John.

"I'm going to get a tattoo," Dean retaliated, "without your permission."

"Hello!"

Dean jumped at the sudden appearance of their waiter. He attempted a nervous chuckle, but when he saw that the waiter was his boyfriend, Castiel, he was so flustered that it came out as a strained cough. He reached for his water glass, still looking at Castiel, and accidentally knocked it over instead. "Ohmygosh I'm so sorry!" he stammered. Sam scooted away from where the water was now dripping onto his lap.

Castiel leaned over the table and scooped the ice back into the glass. He smiled reassuringly. "I'll go get a towel."

Dean dragged his shirt over his nose in embarrassment. "Thanks." Castiel left, and Dean's parents started looking at him funny. Dean groaned and dragged his shirt up over his entire face. He could hear his family laughing. he pulled his shirt back down and sighed.

"What was _that?_ " Sam asked teasingly.

"He startled me!" Dean defended.

Castiel returned with a towel and started wiping down the table. Sam wiped down the seat next to him and gave the towel back to Castiel.

"So, are we ready to order?" he asked, pulling out his booklet.

They all ordered, and his mom informed Castiel that today was Dean's birthday. Dean hid his face in his hands, peeking out through his fingers at Castiel's reaction. Castiel just smiled at him. It was a smile that was just shy of smug. One that said, _oh, I know._ "Birthday boy gets free dessert, his choice."

Dean blushed. Usually, the waiters just brought out a slice of cake and sang "Happy Birthday." He wasn't sure if Castiel was pulling strings because he loved him, or if that was actually the restaurant's policy.

Castiel collected their menus and left. Dean smiled widely in his wake. He couldn't join them for dinner, but at least he was still _here_.

Sam started chatting with their parents about school. Dean didn't participate in the conversation; instead he listened with half an ear as he watched Castiel move around the restaurant. Whenever Castiel glanced over, he smiled softly, and Dean couldn't help but be enamored by it.

"I see that you're feeling better," Mary said, startling him from his haze.

"Uh…" Dean struggled to find words. "There's no point in being sad on my birthday, right?" he said. She scrutinized him from across the table, but in the end she surrendered with a sigh.

"I guess not."

Dean's courage grew after Castiel came by to refill their drinks. "There's something I wanted to tell you guys."

"What is it?" John asked from beside him.

"I'm bisexual," Dean announced. "I like girls and boys."

There was a long pause, and then Sam started laughing. "Oh, is that why you've been checking out the waiter all night?"

"Wha—I have not!"

"Actually, I noticed it too," John said. "You've been glancing in his direction a lot."

"And smiling," Mary added.

"Wow. That was _not_ how I expected you guys to react," Dean said.

"He's been looking over here a lot too," John mused.

"I wonder if he likes boys too," Mary said. "You should ask him."

This was _really_ not how Dean expected his family to react. He had expected them to be at least a little surprised, not try to throw him at the waiter. He squeaked in surprise, and stammered, "I'm going to the bathroom!" He bolted out of his seat and headed towards the bathroom. He didn't even have to go; he just had to take time to process his family's reaction. It was kind of funny really.

When he entered the bathroom, the first person he saw was Castiel washing his hands. A quick look around showed that they were alone.

"Hey, Cas."

Castiel shut off the tap and flicked the water off into the sink. "Hello, Dean."

Dean sidled up to Cas and wrapped his arms around him. "So, is this what you meant when you said things would all work out in the end?"

"Yeah."

"Gotta say, it wasn't what _I_ expected." Dean laid his head on Castiel's shoulder. "I was picturing you coming over to my house after work."

"I get off at nine," Castiel said. Dean lifted his head and kissed his boyfriend. Castiel drew him up in his arms to pull him in closer. They broke the kiss and looked at each other in a warm embrace.

"So, I uh, I just came out to my family," Dean said. Castiel's expression darkened into one of worry.

"How did they take it?" Castiel asked.

Dean groaned, and Castiel's arms tightened around his middle. "They took it _too_ well, man! They're goading me into asking you out." Castiel through his head back laughing. "Stop laughing, you asshole," Dean grumbled.

Castiel wheezed, "I'm sorry, that's just really funny" Dean grumbled some more until Castiel kissed his cheek. "I gotta get back to work, Dean. Can't stay and hold you forever."

"I wish we could," he lamented. Castiel laughed, and Dean reluctantly untangled himself from his arms. "I love you."

Castiel smiled widely and kissed him again. "I love you too, Dean."

Dean waited in the bathroom for a few minutes after Castiel left, to give the illusion that he was actually using the bathroom. When he returned to the table, his family didn't say anything more about Castiel, so Dean assumed that he was in the clear.

 _Boy_ was he wrong.

Later, when Castiel arrived with their food, he gave Dean his last, saying, "And an extra special western burger for the extra special birthday boy." He winked at Dean, and tucked his tray under his arm. Dean blushed and attempted to scowl at Castiel.

"Is there anything else I can get you?" Castiel asked innocently, looking Dean up and down.

"Yeah," Sam piped up, "I wanted to know if you like boys. My brother—ow!" Dean kicked his brother under the table. Sam grinned maliciously and continued, "My brother likes you, but he's too shy to ask." Dean kicked him in the shin again.

Castiel bit his lip and winked at Dean. "I sure do," he said, sauntering off. Dean's face felt sunburnt.

He glared at Sam. "I hate you," he growled, earning a sharp reprimand from his mother.

"I'm just trying to help you out, Dean," Sam said innocently.

"I don't need your help to get a boyfriend!"

"Well, on the bright side, we know he's interested," Mary said unhelpfully.

"He's just pretending," Dean lied. "Waiters who flirt get bigger tips." Dean knew that Castiel wasn't flirting for tips. No, that jerk was being as aggressive as possible to get a rise out of Dean. But he would have none of it.

Dean eventually gave up being embarrassed over his family's attempts to set him up with his own boyfriend and started flirting back just as aggressively. Castiel was cute when he was flustered after all.

When nine o' clock drew near (coincidentally the end of their meal) the waitstaff crowded around their table, plopped down Dean's apple pie a la mode (with a single candle at an increasingly odd angle as the ice cream it was stuck in melted), and started singing "Happy Birthday." Dean blew his candle out, and they al cheered. The majority of them disappeared off to their own portion of the restaurant until only Castiel remained.

"Happy Birthday, Dean," he said, smiling lovingly at Dean.

Dean's chest expanded in affection and grinned back. "Thanks, Cas. Are you coming over later?" He looked at his mom and dad. "Can Cas come over later?" They shared a look of surprise and then nodded.

"Of course, I'd love to come over, Dean," Castiel said.

"Great! I'll text you the address," Dean said.

Castiel leaned over the table, and kissed him gently on the mouth. "Goodnight, Dean. Love you."

"Love you too. See ya later, Cas!" Castiel placed a check on the table and left.

Dean felt giddy at the looks of confusion on his family's faces. He pulled the candle out and licked the ice cream off nonchalantly. "What?"

"I didn't know you two knew each other," John said.

"I told you I didn't need your help getting a boyfriend," Dean said. "We've been dating for like, three months. He reveled in the sheepish looks on their faces and dug into his pie a la mode happily. "At least you didn't try to set me up with a complete stranger."

* * *

 **A/N:** **i wrote this so long ago lol**

 **i've been waiting for dean's birthday and it kinda just snuck up on me today**

 **also it's neary mdinight and i'm so tired**


End file.
